


The radio demons Sugar Baby

by TheGothFanficWriter



Category: Hazbin Hotel (Web Series)
Genre: Alastor is Bad at Feelings (Hazbin Hotel), Alternate Universe - Prostitution, Alternate Universe - Sugar Daddy, Asexual Alastor (Hazbin Hotel), Asexuality Spectrum, Bisexual Vaggie (Hazbin Hotel), Dom/sub Play, Dom/sub Undertones, Dominant Alastor, Dominant Vaggie, Eventual Romance, Eventual Smut, Explicit Language, Explicit Sexual Content, F/M, Falling In Love, First Dates, Fluff and Smut, Kink Discovery, Pegging, Porn With Plot, Praise Kink, Protective Alastor (Hazbin Hotel), Sexual Experimentation, Sexual Inexperience, Submissive Alastor, Submissive Vaggie, Their both switches okay?, Vaggie needs a hug
Language: English
Status: In-Progress
Published: 2021-02-27
Updated: 2021-03-10
Packaged: 2021-03-18 09:29:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,190
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29731824
Author URL: https://archiveofourown.org/users/TheGothFanficWriter/pseuds/TheGothFanficWriter
Summary: After some prompting from Rosie, Alastor gets curious and decides to experiment by taking a sugar baby. He happens to choose a young prostitute by the name of Vaggie, it's the start of an odd romance to say the least.
Relationships: Alastor & Rosie (Hazbin Hotel), Alastor/Vaggie (Hazbin Hotel)
Comments: 15
Kudos: 61
Collections: Wholesome Vagastor Content





	1. Chapter I: Talk dirty

**Author's Note:**

> Look at me starting another work. Ngl a lot of Vagastor smut on here is angsty and I wanted to change that. Plus I wanted to be able to experiment more with Vaggie and Alastors sexual dynamics so here.
> 
> Basically in this universe Charlie never met Vaggie so Vaggie went back to being a prostitute and that's all you really need to know. I might have the happy hotel come up in later chapters but for now just a quick starting chapter

"Come on now Alastor," Rosie said stirring her tea, "I've seen thousands of women take an interest in you, yet you haven't taken a single one to your bed?"

Alastor rolled his eyes, barely listening at this point, "Had no interest in it and afraid I still don't."

"Surely," Rosie scoffed, "No ones caught your eye? Not in your life or afterlife I mean you must at least have been curious enough to have tried."

Alastor shook his head, "What's the point? Relationships are silly anyway."

"Says the man that's never been in one." Roses retorted with a chuckle.

Truthfully Alastor wasn't quite sure what prompted this conversation, he just happened to mention that he never had a partner and all of a sudden Rosie started pushing the subject.

He wasn't that surprised, Rosie having died in the Victorian era had old fashioned views. Though she was rather picky about which modern views she had chosen to adapt to her worldview.

Rosie was quite open minded about homosexual relationships but the idea of no relationship was outright baffling to her.

Alastor sighed, "Rosie. Relationships and sex are just not for me. End of discussion."

"You still haven't answered my question." Rosie said softly, "Truly you've at least wanted to try it at one point? To experiment as the kids call it these days?"

Alastor paused, giving the question some serious thought since Rosie was so insistent about it. He then considered whether he should or should not answer honestly once he had decided.

He had never been fond of this kind of stuff though Rosie quite enjoyed gushing about romance and that mushy stuff. So acting completely uninterested might make her give up but it could also make her more insistent. 

Plus Rosie could normally see through his lies.

"A few times I suppose." Alastor admitted, he was mostly humoring her but he was being somewhat honest.

"I knew it!" Rosie exclaimed, "So what's stopping you? You're Alastor, you could find someone and woo them in no time!"

Alastor rolled his eyes yet again, "Rosie, even if I am a little curious, I've still had no previous relationship experience. The last thing I need is to go out and embarrass myself. I wouldn't know how to 'woo' anyone let alone seduce them."

He was actually being honest, though he had seen films,that was different from doing it in practice. In that sense Alastor was as romantic as sandpaper.

Suddenly, Rosie's smirk shifted into something much more devious.

Alastor raised an eyebrow, "I don't like that look."

"Well Alastor..." Rosie started off, "You could always hire a prostitute-"

"No." Alastor said flatly at the idea, "I'll do no such thing." 

"Come now." Rosie said exasperated, "This is hell. People hire them all the time and you can pay them to keep their mouth shut if things go wrong."

"I'm not resulting to such disgusting means." Alastor scoffed, "Besides. I'd rather not give that rat a single piece of my money."

Rosie would have rolled her eyes if she had pupils, "Not all sex workers work for Valentino." She informed, "Besides..." she continued on, getting out of her chair and picking up a magazine from the other side of the room, "From what I've read you can work out all types of arrangements with these escorts. Some don't even involve sex."

Alastor squinted at the cover of the magazine he had been shown, it had some imp in lewd clothing on the front with bright, outlandish bold letters reading 'Hell's sex life and sex work' along with many crude advertisements to decorate the page.

"Don't know if I'd trust anything out of this book." He said sullenly, "Plus it's the principle of things."

Rosie let out a 'tsk', shaking her head, "Principle? Alastor you barely bathe and eat other demons. Hiring a prostitute won't kill you."

"I need some standards Rosie." Alastor retorted, "I don't see why you care so much anyway."

"I'm your friend. It's my duty to help you." Rosie said, matter of factly. 

"Hmp. Why don't you sleep with me then?" Alastor asked unamused, hoping to deter her.

"Because you wouldn't be able to handle me." Rosie said teasingly, poking Alastors nose. "Just read this and consider it alright? There are all types of whores out there that would just love to spend some time with you."

Alastor gave Rosie a look but took the magazine, "Fine. If it'll shut you up I will read the damn thing but that's no guarantee I'll go through with anything."

"Excellent!" Rosie exclaimed, "If you do decide to meet up with a whore let me know how it goes and if I can recommend a few sections-"

"Stop." Alastor said tucking the magazine underneath his arm, "I came here for some relaxing tea and now that this is over, I intend to get just that." He said picking up his cup again and taking a sip.

"You can be so grumpy at times." Rosie said chuckling, "But mark my words this is the start of something good I just know it!"

Alastor hummed in acknowledgment, quick to change the subject, "So. You and Mimzy are becoming quite close I've noticed."

"You have no idea~" Rosie laughed, immediately beginning to blabber on about it.

Thankfully his love life wasn't brought on for the rest of the conversation.

~~~

Truth be told. Alastor wasn't originally going to read the magazine. But curiosity killed the cat.

After getting done with his overlord duties he started flipping through the page, at first it had been mostly what he had expected.

Lewd images, crude advertisements, and flashy word fonts. Nothing that looked of interest to him.

He almost threw it into a nearby waste bin, until a certain page caught his attention.

It was less flashy than the rest, no advertisements, and also had a list of vocabulary words.

Some he knew, while others were words he had known but apparently had gotten the wrong definition of and some were completely new to him.

Some were more scientific, like, Anorgasmia. The inability to have an orgasm.

Other terms were more vulgar, such as pearl necklace, pegging, bdsm, squirting, rimjob, or jelping. Along with many other things.

Alastors face flushed at the description of some of these words, and at some of the more extreme fetishes listed.

Good lord, if anything of these had been mentioned back in his day you'd be deemed a sexual deviant that needed to be cured.

Though he guessed one of the many terms that surprised him was, "Sugar Daddy"

He had heard it thrown around and assumed it had the same meaning as "pimp" or something but, it seemed to be a bit different from what he expected.

'Sugar Daddy: A man (usually, but not always, older and well-off) who financially supports their partner (can be male or female) in exchange of dates, companionship, or possibly sex.'

Huh. Just paying someone for dates huh? That actually didn't sound too bad.

He recalled Rosie's words, thinking about them more seriously now.

An arrangement without sex, maybe Alastor had he gotten curious enough could lean into that. But finding someone, taking them on dates, having a good time and getting to know them then possibly getting more intimate- again, didn't sound bad.

Alastor had seen dates, in a sense they were similar to outings with friends like he had with Rosie and he often enjoyed those. 

And sex well. Another story on it's own 

Alastors feelings on the matter were complicated to say the least, yet the things listed here......

They were interesting.

He wouldn't act like he found them that exciting but a few them did at least sound kinda fun.

He sighed, not sure quite what he was getting into but proceeded to flip through the pages, learning more and more about a subject that apparently was even more complicated than he thought.

Finally, he sighed, placing the magazine down.

Okay. Maybe Rosie did have a point in this, maybe trying this wouldn't be so bad.

But now lies the question, what lucky prostitute of hell would he choose?


	2. Chapter II: The Whore

**Notes for the Chapter:**

> Ayyyy, didn't forget about this fic. Though updates will be inconsistent but that's all my first for you

Vaggie never liked her line of work. 

She didn't loathe like most and she wasn't forced into it but, she never cared for it. 

It had always been a convenient way to earn cash, and Vaggie had always been in a desperate need of said cash.

Nothing much changed since she arrived in hell.

She tried picking up many different jobs, but unfortunately nothing seemed to make money as fast as spreading your legs did.

She was sure she might make more if she agreed to dance at one of Valentino's clubs or even be his next cam girl but she didn't trust that disgusting pimp for one second. 

Standing on the street corner and making money on her own without any influence was better. 

Besides it was comforting to just have to pretend for one lonely fellow to be the basic dumb slut for cash rather than in front of a camera for the whole world to see.

Granted hell's economy was shit, she still needed a day job along with slut work to get by. Yet, even then she was months behind on rent at risk of getting kicked out every day.

So really....

Nothing really had changed since she arrived in hell.

Just like in life she was a whore barely able to get by, just like in life she was alone and just like in life romance was out of the question. Hell- the closest thing to a romantic relationship ended terribly.

So yeah, the jest was life sucked and Vaggie didn't like her job, but she could live with it. Or....ulive with it? Whatever.

But tonight was difficult for the opposite of reasons.

As she stood at the street corner, along with a few other hookers in their equally slutty outfits, barely any demons came by.

Weird considering Hell's streets were often filled with demons or at least had a few homeless randos laying around. So the quiet night on an empty street was rare to say the least.

"Ugh....this is such shit!" One of the other girls huffed, stomping her high heeled foot. "We get the best business here! Why is it suddenly a ghost town?"

Vaggie couldn't help but chuckle, an oddity in hell was that for the most part other prostitutes seemed to get along well with each other. Vaggie wasn’t close to all the other demoness's, but she had made at least a few friends which was enough.

Frankly Vaggie was internally glad that business had been slow but also aware that she still did need cash for today. Especially if she's gonna face the wrath of her landlord later.

"Calm down now..." another spoke up, one of the whores that Vaggie was actually close to.

Her name was Sakura, a short slim pink deer plant hybrid (for lack of a better word). Honestly she reminded Vaggie a lot of a faun from mythology. She had animal-like legs that were hooved, slender and elegant like a deer but her upper body was more human like, pink smooth skin with the occasional patch of darker pink fur. Her eyes a pale foggy blue with long pastel pink hair, long branches that could easily be mistaken for antlers had cherry blossoms forming off them. 

"I'm sure we'll get someone in a bit, if not, we move a couple of blocks over." Sakura informed calmly, getting a 'tsk' from the other prostitutes.

"You don't think something happened do you?" Vaggie asked suddenly, surprising them.

"Huh. The mute does talk." The other one laughed.

Vaggie rolled her eyes at the comment, it seems not being as chatty as the rest of them warranted plenty of teasing.

"What do you mean?" Sakura asked tilting her head, a few flower petals falling off of her.

"It's just....hell doesn't go quiet for a reason. Maybe something bad happened?" Vaggie suggested with a shrug, "Or maybe someone dangerous is around?"

Sakura hummed, "That is possible..."

"Heh, what would some big ole' dangerous demon what with this place?" Another prostitute chuckled.

"Easy victims." Vaggie suggested dully.

"Huh. If someone comes over here looking for easy prey they ain't gonna get it!" The girl laughed, "I carry a knife around on me for a damn reason and I-"

As the demoness continued to rant Vaggie noticed someone walking up the street, and motioned for Sakura to look, the pink deer have her a questionable look before turning in said direction and her eyes going wide.

"And I- hey! Where are you guys going!?" The demon yelled out confused as they saw the other two rush off, frowning. She turned and also realized who was here and immediately dashed off after them.

So much for all her talk of standing up to fight huh?

Well to be fair, it was the radio demon the three of them were running from and most considered it a normal reaction when he was involved.

The demon almost murdered half of hell on the day of his arrival, God knows what else he could be capable of.

The three girls scrambled off into the nearby abandoned building all keeping themselves hidden, peeking out one of the openings to keep an eye on the overlord.

"What the hell is he doing here!?" Vaggie asked in a hushed tone.

"He never comes around these parts..think he's lookin' for someone?" Sakura asked in a hushed whisper.

"What poor sucker got a meeting with radio demon 'round here?" The other demoness asked just as confused.

Sakura and the other girl began wondering and arguing while Vaggie kept her focus on the radio demon.

She heard of him, the almighty Alastor that had thousands cower and grovel at his feet. The cannibal that ate thousands of innocents and tricked just as many, if not more, into sinister deals with him.

Frankly men like him, made Vaggie sick and unfortunately as much as she wanted to run up then punch him right in his stupid smiling face, she knew better than to start a fight with an overlord. As tempting as it may be.

So far the radio demon looked around, definitely looking for someone. Vaggie watched him closely, maybe he had come to meet up with someone for a deal? What other reasons would he be here for?

While Sakura and the other demoness continued to talk to themselves, Vaggie was slowly putting the pieces together herself.

Let's see.....if it wasn't for a deal then what else? What would a powerful man like Alastor be looking for in this part of the circle? Possible victims?

Vaggie blinked, as she thought of something. 

Could he be....looking for a prostitute? 

She wouldn't doubt that someone like Alastor would use a street whore for cheap entertainment, but from what she heard that didn't sound like Alastor. 

It had been a debate among many about Alastors love life or well, lack of a love life. Many overlords usually had some public relationship, but never Alastor. In fact, he never expressed any interest in men, women or any demon really. Though he clearly had hundreds of demons willing to throw themselves at him.

So, him looking here for an escort, unlikely, but not impossible.

Vaggie shuffled a bit, squinting a bit at Alastor, who still seemed unaware of them hiding. Wonder what he would be like with a street whore? She could imagine him being no different than the usual rich man that got off abusing women and leaving them badly injured, hell he'd probably kill them afterwards rather than actually paying them.

Vaggie should tell the other to run off and ignore the radio demon, but then she remembered how far she was three months behind on rent.

Not just that, but how little cash she had in general. She had some savings but that wouldn't cover the three months behind on rent and even if it did, she have no way to feed herself, get transportation, utilities, clothing, and not even mentioning medicine in case she ever got sick. She was one step away from being on the streets, unless she wanted to be seriously in depth, which in hell, was not a good idea.

Alastor was dangerous but he was rich. She could charge him more than usual and she would be in at least a semi decent financial state. If he attacked her, well she could put up a fight and she did have plenty of weapons, a few even angel weapons, and she could probably run away if worse came to worse.

And....want did she have to lose really?

"We should- Vaggie!?" Sakura called out as Vaggie walked out of the building back into the streets and toward Alastor.

Alastor might not look like it but he was beginning to panic.

After telling Rosie about his decision to give this a try and being ushered over to a spot where he could find a hooker, he was....beginning to regret it. 

No one was here and in all honesty he had no idea how to really approach a prostitute in the first place. Was it similar to just asking for apples at the farmers market? Or was there a certain technique he wasn't aware of? 

Maybe it would have been easier to get a whore from Valentino, but he was nowhere that curious or willing to go to such means. Plus he didn't want to hear any teasing from Val if he learned about this situation.

As some time passed and he considered looking somewhere else or possibly just giving up all together, when he heard someone called out to them.

"Do you need something?"

Quickly, he turned around, raising an eyebrow at who had the bravery to approach him first.

He was oddly delighted at who he saw,

She was short even with her leather high heeled boots, short white hair with pink tips, an eyepatch with a 'X' on it, and wearing a very revealing black and pink leather outfit. Complemented with fishnets and skull earrings.

Not quite his style, but he'll be damned if he didn't find this moth girl cute.

Even if she was glaring at him. 

"Why hello there." He greeted, keeping his natural charisma as always.

"Hi." She said bluntly, "Do you need something?" She repeated a bit more sternly this time.

"I do." Alastor said, tilting his head, "The real question is if you can help me with it."

"Depends..." she said crossing her arms, "Do you wanna fuck me or kill me?"

Alastor blinked, not used to people being so direct, even Rosie tended to word things elegantly when it came to these things.

"Um..." He let out, huh, the radio demon speechless, most wouldn't believe it. Between his own inexperience, secret nervousness and the girl's straightforward attitude, he had no idea how to respond. 

"Well neither really, but uh," he paused, unsure of how to ask for such a thing, one thing was for sure he couldn't risk losing his composure out in the open. "Can we talk somewhere private?"

Vaggie shifted, unsure by this reaction. Was he being....bashful? She wasn't sure if that was the exact word for it but he was certainly acting nervous at least. 

Maybe her assumption had been wrong. It didn't seem like he did this often or possibly he was doing this for the first time. 

That didn't mean she was safe though.

"Sure." She said with a hesitant nod, beginning to follow him as he walked off.

No turning back now it seems.

The best private place Alastor could think of was his limousine. At least it was the most convenient place really.

"Hope you don't mind." He asked, holding the door out for the moth as she shuffled into the limousine, following after her. "Know this isn't the place to conduct business."

"In my profession, you do it in a lot less classier places." Vaggie said dismissively as she settled into one of the car seats.

The limo was nice, though used a lot of red. Seemed to be a common theme with the radio demon.

As Alastor closed the car door behind him, Vaggie spoke up.

"Now look, I cater to a lot of kinks so if you're gonna make me do something ridiculously weird like act like a toddler while spanking you then I will charge extra. But for the most part I'm willing to do almost anything. Nothing involving piss or shit though, that's my one hard-core limit and I'll need some prepping if you want anal-"

Alastor suddenly, very loudly, let out a fit of nervous laughter. Making Vaggie pause.

Okay, this was the first time she ever gotten such a reaction from a client, granted some tended to chuckle when she talked about setting limits but none ever laughed like this.

"Oh! Oh! Um-" Alastor said as his laughter died down, he felt...very awkward and embarrassed right now, "My dear, you see I don't want any of that from you really. Well, not yet is what I mean." 

Vaggie gave him a look, wanting him to continue.

He took a breath, wondering the how to best voice this without sounding perverted or stupid, though honestly he already felt like he had made a fool of himself far too many things.

He should just kill this girl and walk off so she won't tell anyone about how Alastor failed to recruit a sugar baby.

"Now....don't tell anyone this but I don't have any relationship experience." He said finally, "I haven't even had sex. However, I am curious and want to try it, but rushing into something like that- wouldn't work for me." He explained, "I'd rather ease into it. Experience it all slowly, if that makes sense. I'd rather us, well, go on dates and such before jumping into it. I'll of course pay you for all of it, whether you want cash or gifts- or well, other things."

Vaggie paused taking in this information and squinting at him, "So.....you want to be my sugar daddy basically?"

Alastor sighed, "Essentially yes."

Vaggie paused again, taking in this information. Unsureof how to feel about it. 

Alastors lack of love life wasn't too surprising, like said before no one knew anything about Alastors love life or sexual preferences. But the fact he was willing to experiment via prostitution felt surprising for him.

She didn't know, just....if he was such a powerful and rich overlord to buy a street hooker just....didn't feel fitting.

Wouldn't one of Valentino's expensive experienced whores make more sense? Vaggie didn't think she was that attractive and she didn't even have much in terms of experience, yes she did this work for way longer than she would have liked but that was nothing compared to others that did this stuff in hell for centuries.

After a bit she spoke up, "Why me?" She asked finally. "You're Alastor, inexperienced or not, you could have anyone. Meanwhile anyone could have me for a sum of cash."

Alastor chuckled, "Isn't that everyone in your profession?" He asked teasingly, "Truth is, I've had trouble finding people to just simply walk up and talk to on the streets, yet you approached me with little to no fear. I think it's impressive."

Vaggie raised an eyebrow, but shrugged, "Well I'm not one to turn down money. So I'm willing but keep in mind, this is purely business stuff. Don't expect me to catch any feelings."

"Trust me, I wouldn't dream of it." He laughed, before reaching into his coat pocket, "Now we'll talk more about this arrangement later, I have a meeting with the other overlords to attend to, but here's some money for your time." He said handing to her a random wad of cash, not even bothering to count it. "We'll talk more tomorrow, meet me at Devils Diner at eight o'clock."

Vaggie as soon as she was handed the money started counting it, her eye widening at the sight of it all. This had been the most she had ever been paid in her entire career and all she did was talk!

If this were someone else she'd insist this was too much, but she wasn't going to act too considerate around him, especially since he had plenty of money to waste.

Quickly she stuffed the cash into her cleavage, a tight skimpy leather outfit didn't leave room for pockets after all. "See you then I guess," Vaggie said getting up.

"Wait." Alastor said reaching out and grabbing her hand, "How rude of me, I didn't get your name."

Vaggie almost glared at him, but didn't push him away, "Vagatha....but everyone calls me Vaggie." She added on quickly.

Alastor hummed, "What a nice name," he released her hand, "See you soon dear."

Vaggie didn't respond and just left the car.

She sighed to herself as she walked away from it, trying to make out her feelings on what was to come.

**Notes for the Chapter:**

> Vaggies hair is short here for reasons that'll be explained, but mainly I feel like it'd fit the more edgy aesthetic she has here. Also if you couldn't tell Vaggie a lot less morally righteous, so while she doesn't like Alastor (but she will warm up to him eventually) she knows she has no right to judge and tolerates him plus all his bullshit a lot more than she normally would.
> 
> Vaggies not evil but Charlie is the only person that ever pushed her to be good and without her we get a more bitter, reculsive and a bit bitcher Vaggie. 
> 
> Thankfully Alastor is a known lover of bitter treats :p

**Author's Note:**

> Alastor: "I believe I'm awaking to a new kink here"
> 
> Lmao and before anyone ask, Alastor is still ace but he falls more in the grey area of the spectrum. I might explore it more in later chapters.


End file.
